Imidazole → HCID 73014044, compound

HRID 2247492Notes

Reaction equation

HRID 2247492 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.CN(C=O)C.F[C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][C:19]=1[O:26][CH3:27]>C(OCC)(=O)C.O>[N:7]1([C:18]2[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][C:19]=2[O:26][CH3:27])[CH:11]=[CH:10][N:9]=[CH:8]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27373584-Fluoro-3-methoxybenzaldehyde

Product 1

HCID 73014044HCID 73014044, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (2.0 g) and imidazole (662 mg) were added to a DMF (20 mL) solution of 4-fluoro-3-methoxybenzaldehyde (1.50 g). The reaction solution was agitated at 80° C. overnight, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: hexane:ethyl acetate=3:1->ethyl acetate->ethyl acetate:methanol=10:1), and 960 mg of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. customthe organic layer was partitioned
  2. washAfter the obtained organic layer was washed with a saturated saline solution, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (elution solvent: hexane:ethyl acetate=3:1->ethyl acetate->ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-dd9c473346fe475385eddf4449e06096
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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